TY - JOUR
T1 - Direct Synthesis of Polyaryls by Consecutive Oxidative Cross-Coupling of Phenols with Arenes
AU - Dyadyuk, Alina
AU - Sudheendran, Kavitha
AU - Vainer, Yulia
AU - Vershinin, Vlada
AU - Shames, Alexander I.
AU - Pappo, Doron
N1 - Funding Information:
This research was supported by the Israel Science Foundation (Grant No. 164/16).
Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/9/2
Y1 - 2016/9/2
N2 - A bioinspired iron-catalyzed consecutive oxidative cross-coupling reaction between a single phenolic unit and nucleophilic arenes was developed. This sustainable transformation offers a selective synthetic strategy for the preparation of complex polyaryl compounds directly from readily available phenols. With the aid of electron paramagnetic resonance spectroscopy, it was demonstrated that the groups ortho to the phenolic functionality (whether hydrogen, methyl, or methoxy) direct the regioselectivity (ortho, para, or meta via dienone-phenol rearrangement) and chemoselectivity (C-C coupling or C-O coupling) in this multistep process.
AB - A bioinspired iron-catalyzed consecutive oxidative cross-coupling reaction between a single phenolic unit and nucleophilic arenes was developed. This sustainable transformation offers a selective synthetic strategy for the preparation of complex polyaryl compounds directly from readily available phenols. With the aid of electron paramagnetic resonance spectroscopy, it was demonstrated that the groups ortho to the phenolic functionality (whether hydrogen, methyl, or methoxy) direct the regioselectivity (ortho, para, or meta via dienone-phenol rearrangement) and chemoselectivity (C-C coupling or C-O coupling) in this multistep process.
UR - http://www.scopus.com/inward/record.url?scp=84985914686&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.6b02064
DO - 10.1021/acs.orglett.6b02064
M3 - Article
AN - SCOPUS:84985914686
SN - 1523-7060
VL - 18
SP - 4324
EP - 4327
JO - Organic Letters
JF - Organic Letters
IS - 17
ER -